Indole → 3-Chloro-1H-indole

HRID 2036728Notes

Reaction equation

HRID 2036728 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:10]N1C(=O)CCC1=O>CN(C=O)C>[Cl:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 798IndoleHCID 31398Chlorosuccinimide

Product 1

HCID 1777903-Chloro-1H-indoleYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of indole (2.0 g, 17.0 mmol) in DMF (12 mL) at 10° C. under a nitrogen atmosphere was added N-chlorosuccinimide (2.49 g, 18.7 mmol). The reaction was stirred for 4 h then quenched with 10% sodium bisulfite solution. After stirring for 15 min the precipitated solid was collected by vacuum filtration. The filtered solid was washed with water then dissolved in dichloromethane. The solution was washed with water, brine and dried over sodium sulfate then concentrated in vacuo to give 3-chloroindole (1.8 g, 70%) as a yellow-brown solid: 1H NMR (CDCl3, 300 MHz) δ 8.06 (s, 1H), 7.64 (d, J=7.8 Hz, 1H), 7.34-7.37 (m, 1H), 7.16-7.22 (m, 2H).

Workup

  1. customthen quenched with 10% sodium bisulfite solution
  2. stirringAfter stirring for 15 min the precipitated solid
  3. filtrationwas collected by vacuum filtration
  4. washThe filtered solid was washed with water
  5. dissolutionthen dissolved in dichloromethane
  6. washThe solution was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-86734a97e681445eb9051d756bfe1cfd
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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